Sulfonic Acid-Catalyzed Autoxidative Carbon-Carbon Coupling Reaction under Elevated Partial Pressure of Oxygen

Authors

  • Áron Pintér,

    1. Max-Planck-Institut für Kohlenforschung, Kaiser-Wilhelm-Platz 1, 45470 Mülheim an der Ruhr, Germany, Fax: (+49)-208-306-2980
    2. Present address: Institute of Organic Chemistry, University of Duisburg–Essen, Universitätsstr. 7, 45117 Essen, Germany
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  • Martin Klussmann

    Corresponding author
    1. Max-Planck-Institut für Kohlenforschung, Kaiser-Wilhelm-Platz 1, 45470 Mülheim an der Ruhr, Germany, Fax: (+49)-208-306-2980
    • Max-Planck-Institut für Kohlenforschung, Kaiser-Wilhelm-Platz 1, 45470 Mülheim an der Ruhr, Germany, Fax: (+49)-208-306-2980
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Abstract

An aerobic organocatalytic oxidative C[BOND]C bond formation reaction of benzylic C[BOND]H bonds with various C-nucleophiles is described. The coupling reaction proceeds by simply stirring the substrates under elevated partial pressure of oxygen in the presence of a sulfonic acid catalyst at room temperature. Elevation of the pressure enables the reaction of a broad scope of nucleophile substrates otherwise showing poor reactivity at ambient pressure. The benzylic C[BOND]H bonds of xanthene, acridanes, isochromane and related heterocycles could be functionalized with nucleophiles including ketones, 1,3-dicarbonyl compounds and aldehydes. Electron-rich arenes could be utilized as nucleophiles at elevated temperatures. The reactions are believed to proceed via autoxidation of the benzylic C[BOND]H bonds to the hydroperoxides and subsequent nucleophilic substitution catalyzed by sulfonic acids.

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